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Construction of Carbo- and Heterocycles Using Radical Relay Cyclizations Initiated by Alkoxy Radicals

TitleConstruction of Carbo- and Heterocycles Using Radical Relay Cyclizations Initiated by Alkoxy Radicals
Publication TypeJournal Article
Year of Publication2009
AuthorsZhu, H, Wickenden, JG, Campbell, NE, Leung, JCT, Johnson, KM, Sammis, GM
JournalOrganic Letters
Volume11
Pagination2019-2022
Date PublishedMay
Type of ArticleArticle
ISBN Number1523-7060
Keywords1, 5-HYDROGEN ATOM TRANSFER, AMPHIDINOLIDE K, C-H ACTIVATION, CARBONYLATION, CHAIN REACTIONS, EFFICIENT, FUNCTIONALIZATION, ORGANIC-SYNTHESIS, REARRANGEMENT, TRANSLOCATION REACTIONS
Abstract

An efficient method for the rapid construction of carbo- and heterocycles has been developed using radical relay cyclizations initiated by alkoxy radicals. Linear substrates were cyclized to form a wide range of cyclopentane, pyrrolidine, tetrahydropyran, and tetrahydrofuran derivatives in excellent yields. This methodology was utilized as a key step in the synthesis of the tetrahydrofuran fragment in (-)-amphidinolide K.

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